How to Bring a Problem to Your Boss (Without Looking Helpless)

Three different times today, you’ve made your way to your boss’ door, paused before knocking, and then just decided to turn around altogether. You’ve drafted and then promptly deleted five separate emails. You awkwardly loitered behind your manager at the coffee pot, willing yourself to speak up.

Why? Well, you have a work-related issue that’s been plaguing you all day. And, on top of that, you have another problem: You have no clue how to actually deal with it.

You want to approach your supervisor to get her advice on how you should proceed. However, you also don’t want to seem like a fumbling idiot who’s incapable of handling even the smallest roadblock.

All of the career advice you’ve read taunts you with this one sentiment:

Come up with a potential solution that you can bring to your boss for approval.

That strategy is great—provided you have any clue where to get started. But, you? You’re totally lost. You have no idea how to even begin resolving this issue, meaning the idea of coming up with a suggestion on your own is pretty much a pipe dream.

So, what do you do? How can you bring this problem to you boss, without seeming totally helpless and incompetent? Follow these five steps.

1. Determine Your Method

First things first, you need to determine how you should approach your manager. Will you send an email or have this conversation in-person?

The lure of email can be tempting, especially since it saves you the embarrassment of needing to look your boss in the face as you confess your own perceived stupidity. Fortunately, jotting your supervisor a message can work just fine for any non-urgent matters. Plus, email gives you the opportunity to document any information that your boss might require (more on that in a minute!).

But, if this problem you’re dealing with is particularly time-pressing or groundbreaking? Much like any other serious conversation, those issues are best handled face-to-face.

2. Gather Your Facts

Imagine that you strolled into your manager’s office and nonchalantly said, “Hey, boss! The building is on fire and I was really hoping you could jump in and put it out.”

Your manager is bound to have questions. How did this fire get started? Has anybody already tried to put it out? Why is this happening?

Just because you can’t bring any potential solutions to your supervisor doesn’t mean that you can wander into his office without any context. He’ll need the necessary background information in order to better understand the situation and help you identify the best way forward.

Before initiating the conversation, take some time to think through the entirety of your problem:

What conversations or circumstances led you to this point?

Did you make any mistakes that exacerbated this issue?

Are there any other players involved that your manager should be aware of?

Is there any documentation your boss will need to get a better understanding of the whole picture?

Coming armed and ready with all of this information in place will show that you aren’t just aiming for an easy way out of your sticky situation. You may not have the answer—but at least you took the time to gather the facts.

3. Explain the Potential Fallout

There’s a reason that you’re going to your boss with this problem—not only because you don’t have the solution, but also because you know that making the wrong move could have some serious consequences.

You need to make that potential fallout explicitly clear. What makes this problem worthy of his time and attention? Is a client really angry? Is the company’s reputation at risk?

More often than not, managers prefer to get involved before stuff really hits the fan. So, your own supervisor will likely be happy that you brought the issue to him before things turned into even a bigger mess.

4. Resist the Urge to Apologize

Not having the answer can be a blow to your ego. But, cut yourself some slack and remind yourself of the fact that—whether you’re new or well-established in your position—you’re not supposed to know everything. It’s for that very reason that you have a boss to guide and advise you when these sorts of things come up.

As embarrassed as you might feel, don’t fall into the trap of repeatedly apologizing for what you assume to be your own ignorance. Instead, be matter-of-fact about the help that you need and express gratitude for your manager’s insights.

What does that look like? Instead of saying:

“I’m really sorry that I need to bother you with this. I just don’t know what to do.”

Try something like this:

“I’d really appreciate your help in figuring out the best way to respond to this client.”

5. Take Notes

Not knowing how to resolve something once is totally understandable and forgivable. But, if you continue to repeatedly approach your boss with that exact same issue, you’re bound to begin fostering that helpless reputation you’re so desperately trying to avoid.

When your manager does walk you through how to solve the problem that’s on your plate, make sure you document it. Create yourself a little cheat sheet where you can record the answers to questions and issues you might see crop up again.

That way, if you encounter that issue in the future, you’ll be able to take a little more initiative on your own.

Needing to approach your boss with a problem can definitely poke holes in your confidence—and, even more so when you don’t have any ideas for how to address that setback yourself.

However, it happens. You don’t have all of the answers, and every now and then you’ll need to lean on your manager’s experience and wisdom to get you through some sticky situations.

So, take a deep breath, follow these five steps, and finally knock on your boss’ door. I’m willing to bet you’ll be pleasantly surprised by how that conversation plays out.

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Kat is a Midwest-based freelance writer, covering topics related to careers, self-development, and the freelance life. In addition to writing for The Muse, she's also the Career Editor for The Everygirl, a columnist for Inc., and a contributor all over the web. When she manages to escape from behind her computer screen, she's usually babying her rescued terrier mutt or continuing her search for the perfect taco. Say hi on Twitter @kat_boogaard or check out her website.